The instant invention relates to alkyl-substituted spiroundecenone derivatives defined according to the structure: ##STR2## wherein R.sub.1 represents isopropyl or hydrogen and R.sub.2, R.sub.3 and R.sub.4 are each the same and each represents methyl or hydrogen; with the provisos:
(i) that when R.sub.1 is isopropyl, R.sub.2, R.sub.3 and R.sub.4 are hydrogen; and PA1 (ii) when R.sub.2, R.sub.3 and R.sub.4 are methyl, R.sub.1 is hydrogen,
and uses of same in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
Inexpensive chemical compounds which can provide woody, fruity, fresh minty, sweet, floral, herbaceous, spicy and celery aromas with pepper and geranium topnotes and tagette-like undertones are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfume compositions as well as perfumed articles are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to find synthetic materials which will replace, enhance or augment the fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree or they contribute undesirable or unwanted odor to the compositions.
Spiro ketones including spiroundecenones are known in the prior art and their utilities are known in perfumery.
Thus, Japanese Published Application No. 76/65738 (abstracted at Chemical Abstracts 85: 123440f) (corresponding to U.S. Pat. No. 4,052,457 issued on Oct. 4, 1977) discloses the compound having the structure: ##STR3## as being useful in perfumery and further discloses the process according to the reaction: ##STR4##
Nerdel and Dahl, Ann. Chim., 710, 90 (1967) discloses the compound having the structure: ##STR5## and the generic process, to wit: ##STR6## (wherein R represents hydrogen or methyl).
Tanaka, et al, Chem.Comm. 1967, page 188 (title of paper: "The Total Synthesis of Chamigrene" discloses the compound having the structure: ##STR7##
U.S. Pat. No. 4,261,866 issued on Apr. 14, 1981 discloses the genus of compounds having the structure: ##STR8## wherein R.sub.1 -R.sub.6 each represents hydrogen or lower alkyl. U.S. Pat. No. 4,261,866 further discloses the broad genus, to wit: ##STR9## wherein each of the dashed lines represent carbon-carbon single bonds and carbon-carbon double bonds. The compounds disclosed in U.S. Pat. No. 4,261,866 are indicated to be useful in perfumery.
However, the alkyl-substituted spiroundecenone derivatives of our invention have unexpected, unobvious and advantageous perfumery properties when compared with the perfumery properties of the above-cited prior art.